[UncleSam]

> I am currently plugged into my monitor which is providing power + USB. I didn't have to try three times to plug it in.

Unrelated to the plug orientation, occasionally my laptop fails to properly connect to my monitor over USB C (providing both data and power) until I have plugged it in several times. The issue could be either the monitor, laptop, or cable. This is just anecdata, but it shows how USB C alone hasn't solved the problem where it doesn't just work the first time.